tert-Butyl(2-iodoethoxy)dimethylsilane

Cat.NO.:A108333 Purity:97%

Product Details of [ 101166-65-8 ]

CAS No. :	101166-65-8
Formula :	C₈H₁₉IOSi
M.W :	286.23
SMILES Code :	C[Si](OCCI)(C(C)(C)C)C
MDL No. :	MFCD09909940
InChI Key :	CAAUZMMMFDVBFD-UHFFFAOYSA-N
Pubchem ID :	11129873

Safety of [ 101166-65-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 101166-65-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	0
Fraction Csp3	1.0
Num. rotatable bonds	4
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	62.49
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	9.23 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.09
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.96
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.44
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.84
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.51
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.97

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.85
Solubility	0.0409 mg/ml ; 0.000143 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.85
Solubility	0.04 mg/ml ; 0.00014 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.46
Solubility	0.0983 mg/ml ; 0.000344 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.23 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	3.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12’782’590 molecules and tested on 40 external molecules (r² = 0.94)	4.2

Application In Synthesis of [ 101166-65-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 101166-65-8 ]

[ 101166-65-8 ] Synthesis Path-Downstream 1~35

1
[ 75-21-8 ]
[ 18162-48-6 ]
[ 101166-65-8 ]

References: [1]Synthesis,1991,p. 1231 – 1235.

2
[ 15925-47-0 ]
[ 101166-65-8 ]
[ 88939-06-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 121 – 130.
[2]Tetrahedron Letters,1983,vol. 24,p. 5143 – 5146.

3
[ 3406-02-8 ]
[ 101166-65-8 ]
[ 132785-45-6 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 6819 – 6822.

4
[ 101166-65-8 ]
[ 105550-54-7 ]
tert-Butyl-[3-(4-chloro-phenylsulfanyl)-hexa-3,4-dienyloxy]-dimethyl-silane [ No CAS ]

References: [1]Journal of the Chemical Society. Chemical communications,1986,p. 941 – 942.

5
[ 101166-65-8 ]
[ 101166-64-7 ]
[ 101166-66-9 ]

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 1571 – 1574.

6
[ 101166-65-8 ]
[ 137627-17-9 ]
1-(tert-Butyl-dimethyl-silanyl)-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-trimethylsilanyloxy-azetidin-2-one [ No CAS ]

References: [1]Journal of the Chemical Society. Chemical communications,1989,p. 1448 – 1449.

7
[ 101166-65-8 ]
[ 121846-23-9 ]
[ 121846-24-0 ]

References: [1]Journal of the American Chemical Society,1989,vol. 111,p. 4997 – 4998.

8
[ 101166-65-8 ]
[ 144760-70-3 ]
1-<2′-<<(tert-Butyl)dimethylsilyl>oxy>ethyl>-1-azacyclotetradecan-2,14-dion [ No CAS ]

References: [1]Helvetica Chimica Acta,1994,vol. 77,p. 819 – 828.

9
[ 89031-81-2 ]
[ 101166-65-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium iodide; In acetone; at 120℃; for 4h;Inert atmosphere; Sealed tube; Microwave irradiation;	A solution of TBSCl (30.1 g, 200 mmol) in DCM (50 mL) was added dropwise over 15 min to a stirred solution of 2-chloroethanol (16.0 g, 200 mmol), imidazole (20.4 g, 300 mmol) and DMAP (0.244 g, 2.0 mmol) in DCM (200 mL) at 0 °C under an argon atmosphere, and the resulting mixture was warmed to room temperature where it was stirred for 12 h. The mixture was quenched with saturated aqueous NH4Cl (200 mL) and the separated aqueous layer was then washed with DCM (2*100 mL). The combined organic extracts were washed with saturated aqueous NH4Cl (100 mL) and brine (100 mL), then dried over MgSO4 and concentrated to leave 2-chloroethoxy tert-butyl dimethylsilane (37.1 g, 95percent) as a colourless oil. A solution of the silyl ether (3.88g, 20.0mmol) and sodium iodide (8.94g, 60 mmol) in acetone (10mL) was sealed in a microwave vial and heated at 120°C for 4h in a microwave reactor. The vial was cooled to room temperature and the reaction mixture was then diluted with diethyl ether (80mL) and filtered through silica. The filtrate was concentrated to leave 2-iodoethoxy tert-butyl dimethylsilane (5.72g, quant.) as a pale yellow oil, which was used without further purification. A solution of methyl acetoacetate (2.55g, 22.0mmol) in 79 THF (10mL) was added over 10 min to a stirred suspension of sodium hydride (0.88g, 22.0 mmol, 60percent) in THF (50mL) at 0°C under argon. The mixture was stirred for 15 min, and then a solution of n-butyl lithium (11.0 mL, 22.0 mmol, 2.0M in hexane) was added dropwise over 10 min and the mixture was stirred at 0°C for 15 min. A solution of the above, crude iodide (ca. 20 mmol) in THF (10 mL) was added dropwise over 10 min, and the resulting yellow mixture was then warmed to room temperature where it was stirred for 12 h. The mixture was quenched with saturated aqueous NH4Cl (100 mL) and diethyl ether (100mL), and the separated aqueous layer was then washed with diethyl ether (2×100mL). The combined organic extracts were washed with brine (100 mL), then dried over MgSO4 and concentrated to leave a pale yellow gum. Purification by column chromatography (25:1, petrol/Et2O) gave the keto ester (5.05 g, 77percent) as a pale yellow oil (10percent enol form): deltaH (400 MHz, CDCl3) 3.73 (3H, s, CO2CH3), 3.61 (2H, t, J=6.0, CH2O), 3.46 (2H, s, CH2), 2.62 (2H, t, J=7.1, CH2C(O)), 1.80 (2H, tt, J=6.0, 7.1, CH2), 0.87 (9H, s, SiC(CH3)3), 0.03 (6H, s, SiCH3); deltaC (100 MHz, CDCl3) 202.6 (C=O), 167.6 (CO2CH3), 61.8 (CH2O), 52.2 (CO2CH3), 49.0 (CH2), 39.4 (CH2), 26.5 (CH2), 25.9 (SiC(CH3)3), 18.2 (SiC(CH3)3), ?5.4 (2×SiCH3); HRMS m/z C13H26O4SiNa+ (MNa+) requires 297.1498, found 297.1498.

References: [1]Tetrahedron,2014,vol. 70,p. 7229 – 7240.
[2]Journal of the Chemical Society. Perkin transactions I,1988,p. 1417 – 1424.

10
[ 101166-65-8 ]
[ 105-45-3 ]
[ 116585-05-8 ]

Yield	Reaction Conditions	Operation in experiment
77%		A solution of TBSCl (30.1 g, 200 mmol) in DCM (50 mL) was added dropwise over 15 min to a stirred solution of 2-chloroethanol (16.0 g, 200 mmol), imidazole (20.4 g, 300 mmol) and DMAP (0.244 g, 2.0 mmol) in DCM (200 mL) at 0 °C under an argon atmosphere, and the resulting mixture was warmed to room temperature where it was stirred for 12 h. The mixture was quenched with saturated aqueous NH4Cl (200 mL) and the separated aqueous layer was then washed with DCM (2*100 mL). The combined organic extracts were washed with saturated aqueous NH4Cl (100 mL) and brine (100 mL), then dried over MgSO4 and concentrated to leave 2-chloroethoxy tert-butyl dimethylsilane (37.1 g, 95percent) as a colourless oil. A solution of the silyl ether (3.88g, 20.0mmol) and sodium iodide (8.94g, 60 mmol) in acetone (10mL) was sealed in a microwave vial and heated at 120°C for 4h in a microwave reactor. The vial was cooled to room temperature and the reaction mixture was then diluted with diethyl ether (80mL) and filtered through silica. The filtrate was concentrated to leave 2-iodoethoxy tert-butyl dimethylsilane (5.72g, quant.) as a pale yellow oil, which was used without further purification. A solution of methyl acetoacetate (2.55g, 22.0mmol) in 79 THF (10mL) was added over 10 min to a stirred suspension of sodium hydride (0.88g, 22.0 mmol, 60percent) in THF (50mL) at 0°C under argon. The mixture was stirred for 15 min, and then a solution of n-butyl lithium (11.0 mL, 22.0 mmol, 2.0M in hexane) was added dropwise over 10 min and the mixture was stirred at 0°C for 15 min. A solution of the above, crude iodide (ca. 20 mmol) in THF (10 mL) was added dropwise over 10 min, and the resulting yellow mixture was then warmed to room temperature where it was stirred for 12 h. The mixture was quenched with saturated aqueous NH4Cl (100 mL) and diethyl ether (100mL), and the separated aqueous layer was then washed with diethyl ether (2×100mL). The combined organic extracts were washed with brine (100 mL), then dried over MgSO4 and concentrated to leave a pale yellow gum. Purification by column chromatography (25:1, petrol/Et2O) gave the keto ester (5.05 g, 77percent) as a pale yellow oil (10percent enol form): deltaH (400 MHz, CDCl3) 3.73 (3H, s, CO2CH3), 3.61 (2H, t, J=6.0, CH2O), 3.46 (2H, s, CH2), 2.62 (2H, t, J=7.1, CH2C(O)), 1.80 (2H, tt, J=6.0, 7.1, CH2), 0.87 (9H, s, SiC(CH3)3), 0.03 (6H, s, SiCH3); deltaC (100 MHz, CDCl3) 202.6 (C=O), 167.6 (CO2CH3), 61.8 (CH2O), 52.2 (CO2CH3), 49.0 (CH2), 39.4 (CH2), 26.5 (CH2), 25.9 (SiC(CH3)3), 18.2 (SiC(CH3)3), ?5.4 (2×SiCH3); HRMS m/z C13H26O4SiNa+ (MNa+) requires 297.1498, found 297.1498.

References: [1]Tetrahedron,2014,vol. 70,p. 7229 – 7240.
[2]Journal of the Chemical Society. Perkin transactions I,1988,p. 1417 – 1424.

11
[ 101166-65-8 ]
[ 693-02-7 ]
[ 96475-79-5 ]

References: [1]Synthesis,1991,p. 1231 – 1235.

12
[ 101166-65-8 ]
[ 2321-07-5 ]
C₂₈H₃₀O₆Si [ No CAS ]

References: [1]Journal of the American Chemical Society,1988,vol. 110,p. 301 – 303.

13
[ 101166-65-8 ]
[ 135513-92-7 ]
(2R,3R)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-3-hydroxy-pentanoic acid tert-butyl ester [ No CAS ]
(2R,3S)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-3-hydroxy-pentanoic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,1995,vol. 60,p. 3576 – 3577.

14
[ 108-24-7 ]
[ 101166-65-8 ]
[ 159213-03-3 ]
Acetic acid (1S,2S)-2-[((R)-4-acetoxy-2-methyl-butyryl)

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